Sex. Celebrity. Politics. With Teeth
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Sex. Celebrity. Politics. With Teeth

Anna Wintour Is an O.G. Fashion Troll

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Anna Wintour did something a little unusual last week at the White House state dinner: she reached deep into her no doubt capacious closet, and fished out a Chanel haute couture gown she last publicly wore three years ago. To another high-profile event — the Met Ball, which she organizes. That was far from the Vogue editor-in-chief's first incursion into the normal-person practice of outfit repeating. In fact, she's been doing it for years. Often she repeats an outfit several times in one season, but sometimes her repeats are a little more ambitious. Why, just last month, Wintour wore a five-year-old dress to an event for the Human Rights Campaign. Why would someone who receives a rumored annual clothing budget of $200,000 as part of her compensation package from Condé Nast bother outfit-repeating? Fucking Christ, people, she's Anna Wintour. She can wear whatever the hell she wants. If she never wants to take off her favorite Prada snakeskin coat ever, ever, ever again, she doesn't have to. Besides, I bet she really enjoys trolling us all.

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L-R: September 24, 2009; September 21, 2009; October 1, 2009.

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L-R: November 15, 2010; January 19, 2011; March 5, 2011; September 26, 2010.

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L-R: April 29, 2009; September 10, 2010.

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L-R: May 4, 2009; March 14, 2012.

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Wintour likes this printed dress so much she's not only worn it several times, but owns it in at least two colors. L-R: September 8, 2011; September 22, 2011; September 29, 2011.

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L-R: July 5, 2011; September 6, 2011; September 29, 2011.

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L-R: May 16, 2011; June 10, 2011; September 9, 2011.

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Wintour often wears the same light brown suede boots. She often wears them with her same favorite fur coats. L-R: February 15, 2011; February 25, 2011; February 11, 2012; February 25, 2012.

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In fact, Wintour has worn those boots consistently since 2000.

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She also has them in black. L-R: March 16, 2009; February 13, 2011; February 21, 2011; February 20, 2012.

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L-R: May 27, 2008; August 25, 2008; September 10, 2008.

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L-R: July 6, 2007; February 4, 2012; November 17, 2008; April 29, 2009.

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L-R: September 14, 2005; September 16, 2005; July 5, 2010; August 30, 2010.

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L-R: January 25, 2011; February 13, 2011; September 13, 2011; September 24, 2010.

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L-R: September 7, 2010; September 21, 2010; June 13, 2011; July 7, 2011.

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Anna Wintour's most frequently repeated accessory by far, however, is her favorite pair of shoes, which she wears with all manner of outfits, practically year-round. Her taupe leather low-heeled Manolo Blahnik sandals have been a ubiquitous part of her wardrobe for nearly two decades. Last year, Blahnik told the press he has made several personalized lasts of Wintour's feet just so she can re-order these sandals. Center photo: September 14, 2006.